Cu-catalyzed asymmetric 1,4-addition of Me3Al to nitroalkenes. Synthesis of (+)-Ibuprofen

Polet, Damien; Alexakis, Alexandre

doi:10.1016/j.tetlet.2005.01.007

Scientific article

Letter

English

Cu-catalyzed asymmetric 1,4-addition of Me3Al to nitroalkenes. Synthesis of (+)-Ibuprofen

ContributorsPolet, Damien; Alexakis, Alexandre

Published inTetrahedron letters, vol. 46, no. 9, p. 1529-1532

Publication date2005

Abstract

Trimethylaluminium undergoes enantioselective (ee up to 93%) copper-catalysed Michael addition to various nitroalkenes. Copper thiophenecarboxylate (CuTC) (2 mol %) and 4 mol % of a chiral phosphoramidite ligand are sufficient for a complete and clean reaction. The synthesis of (+)-ibuprofen is described with 82% ee.

Keywords

Copper
Aluminium
Nitro
Conjugate addition
Asymmetry
Ibuprofen

Affiliation entities

Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Citation (ISO format)

POLET, Damien, ALEXAKIS, Alexandre. Cu-catalyzed asymmetric 1,4-addition of Me3Al to nitroalkenes. Synthesis of (+)-Ibuprofen. In: Tetrahedron letters, 2005, vol. 46, n° 9, p. 1529–1532. doi: 10.1016/j.tetlet.2005.01.007

Article (Published version)

Identifiers

PID : unige:8123
DOI : 10.1016/j.tetlet.2005.01.007

Journal ISSN0040-4039

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Cu-catalyzed asymmetric 1,4-addition of Me3Al to nitroalkenes. Synthesis of (+)-Ibuprofen

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